2-Methyl-2-butene → HCID 22728132, compound

Participants

Reaction Steps

To a solution of 5-(2,6-dimethyl-4-nitro-phenoxy)-2-methoxy-benzaldehyde (6.6 g, 21.8 mmol) and 2-methyl-2-butene (23.0 g, 327 mmol) in a mixture of tetrahydrofuran (31 mL) and t-butyl alcohol (210 mL) at room temperature was added dropwise a solution of sodium chlorite (17.7 g, 196 mmol) in KH2PO4 (0.6 M, 254 mL). The resulting mixture was stirred at room temperature for 16 hours, and then saturated aqueous Na2S2O3 (100 mL) was added. The solution was stirred at room temperature for 30 minutes and extracted with ethyl acetate (3 times 300 mL). The combined organic extracts were dried over Na2SO4 and concentrated to afford the title compound (7.7 grams) as a crude product. The product was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ8.01 (s, 2H), 7.49 (s, 1H), 7.02 (s, 2H), 4.06 (s, 3H), 2.19 (s, 6H). MS (APCI−) Calc: 317.3, Found: 316.3 (M−1).

Provenance & Evidence